This article illuminates the unique intersection of Jewish pedagogy and aesthetics in the religious thought of Mendelssohn’s Bi’ur. First, it shows that the didactic mediation of sublime beauty in Biblical Hebraic poetry was a chief motivation of Mendelssohn’s Bi’ur. By drawing on the special aesthetic qualities of Hebraic poetry, Mendelssohn believes he can decisively prove the cultural advantage of the Jewish tradition over other high European cultural traditions. Then, the article discusses Mendelssohn’s recourse to Jewish Hellenistic sources in relation to his understanding of Biblical poetry. The study emphasizes his reading of the Song of the Well (‚Shirat ha-Be’er‘, Num 21,17–18), which draws on Philo of Alexandria’s text ‚De vita Moysis‘. It is in connection with this that the article reveals a hitherto unknown Christian source of Mendelssohn’s Torah commentary. Finally, the article suggests, with reference to the oft-cited source of the Bi’ur, namely Azariah de’ Rossi’s ‚Light of the Eyes‘, that Mendelssohn’s aesthetic perception of Judaism could have been shaped by Philo’s ‚De vita contemplativa‘, which depicts the religious ceremonies of the Jewish Alexandrian sect of the Therapeutae. Altogether, these three thematic steps uncover the high degree of innovation and textual reception characteristic of Mendelssohn’s religious pedagogy when he wrote his Biblical commentaries.